Thanks again to all who posted. It's been very insightful and your advice does ring true of the ESTJ's in my family. A few things:
1) Stuff definitely is rolling down hill. His bosses are all over him. And we try to keep that in mind.
2) IzThe411 hit the nail on the head about his nitpicking about things "that don't really have a huge impact on the final results." It's little stuff. That's what's maddening to me. INTP's are really good at seeing how everything is working together - we see how it all comes together. While he is spending 10 minutes arguing with someone about "how long their method takes", I'm just listening to it all and thinking to myself, "Are you forgetting that you're wasting 10 minutes RIGHT NOW of your own time and of that person's time - that's actually 20 minutes. And what's even more maddening is that sometimes he'll be arguing with one of the most productive workers that he has - the person who gets stuff done the fastest. It's like he's so focused on trying to tell people that they're wrong, that he's getting in his own way - stepping on his own feet. He ends up being the one who is wasting everyone's time. The person is already EXTREMELY fast and good - why change a good thing?
3) As for his questions meaning "State your case. Show me I'm wrong." This is what drives an INTP nuts. Because we've already analyzed (probably 10 times more than he has) what is the ABSOLUTE most efficient way to do it. We're INTP's - that's what we do. I know that he doesn't know that, but it's like he's challenging me on things like "why I'm using the wrong brand of tissue" (I'm exaggerating), when I've already got it worked out - my bottom line results are good.
If I have a productive worker who gets things done quickly and efficiently, I'm leaving that person alone and letting them "do what they do". It's like if you peek into your kid's bedroom and he's cleaning his bedroom all by himself. He's putting things in their right place, being very productive. You're not going to interrupt him. Let him keep doing it - and then when he's all done, maybe you tell him "good job" or you reward him in some way. You wouldn't say, "You put that toy in the left side of the toy box. I want it on the right side from now on."
Just the way I see it. But, thanks again for the ESTJ insight.